Rachel Roams | Chicago, IL: Travel Guide

 

Chicago is a city on a lake, a city of full of history, and a city of neighborhoods, each rich in diversity, charm, and personality, and each worth exploring. It's big, uncompromising, and every corner has a story.

A city lauded for it's dinging and drinking culture, one that would satisfy even the lustiest of appetites, Chicago's stunning architecture and friendly locals make this city a go-to for any weekend getaway. Honestly... I haven't fallen this hard for a city since I decided to move to Phoenix.

After my week in Phoenix apartment hunting, my friend and fellow photographer Brookklyn and I traveled to Chicago for a wedding we were shooting and with two days to spare we decided to explore.

DAY ONE

LODGING

Maybe the first thing you don't think about when planning a weekend in Chicago is staying in a hostel, but maybe it should be. Holiday Jones joins the new breed of hostels that are smashing the outdated stereotypes they've held in the past with trendy decor, modern technology, planet-friendly practices and most importantly, fun opportunities to meet new people-which is really what traveling is all about.

Conveniently and centrally located in the creative Wicker Park neighborhood, a stay at Holiday Jones provides an affordable alternative to your Windy City stay.

 
 
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Marble tables, window benches and complimentary wifi provide nice working spots in the hostels corridors and in just about every room there is a fun selection of classic comic book type posters on the walls.

 
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Brookklyn and I checked in and freshened up in our own private room and after a quick change of clothes, away we wandered to shake off our jet lag.

 
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DO

Brookklyn and I both identify with what we once heard coined “maximizers”: those who like to “maximize” their time by squeezing the most out of every opportunity and experience, relentless and uncompromising until we’ve tried it all. Traveling together, we've come to excel at scouting out "the best" in an attempt to avoid wasting a meal on mediocrity or gamble missing out on something truly monumental.

For any maximizer, FOMO is as real and unpleasant as razor burn. So when we heard about all the neighborhoods that make up the city of Chicago, we planned to see them all-in two days. And we did.

NOTABLE NEIGHBORHOODS

THE LOOP

Every year, millions flock to Chicago and are content to spend the entirety of their visit in the Loop. Past visits to the "Windy City" have left me guilty of this and while there's so much more to the city as I found out this time around, I will admit that there is something captivating about the towering skyscrapers and pieces of public art that populate the dense downtown area. If you head to the loop, make sure to explore the world's best in museums by visiting the Art Institute or relaxing in the city's "front yard" as you stroll through Grant Park.

CHINA TOWN

Located roughly three miles from downtown Chicago, Chinatown is a small, vibrant neighborhood filled with locals and tourists alike. With breathtaking architecture, from the towering bright red gate on Wentworth Avenue to tranquil Ping Tom Memorial Park along the Chicago River, this neighborhood is a must-see in Chicago. Most come for the authentic cultural cuisine but there is so much more to explore like the American Museum, or the annual Chinese Lunar New Year Parade, when the streets line up with dragons and drummers alike.

BOYSTOWN

The party never stops in Boystown, and the Chicago neighborhood boasts one of the largest LGBT communities in the United States. With a flourishing stage show scene and lively nightlife, Boystown offers a plethora or restaurants, thrift stores and boutique (mostly men's) clothing stores.

NORTH LAWNDALE

This neighborhood is still recovering from decades of disinvestment and failed urban policies. Its streets are lined with dilapidated historic mansions, stately greystones that in their former glory must have been a sight to behold, and ex-synagogues recalling its past as a Jewish community. The real sight seeing excursion for us was a first hand glimpse at the famous Gallagher house from the hit showtime tv show Shameless. While we didn't stop for pictures, it's said albeit unconfirmed that the owner of this house does tolerate pictures on the front porch in exchange for a $5 donation.

WICKER PARK

If you have an acute knowledge of palate pleasing nightcaps or an affinity for locally sourced coffee there is no better neighborhood to sip and shop in Chicago than Wicker Park. This creative epicenter of Chicago is also advertised as one of the most sought after, Michelin-rated dining scenes. Its also home to an unbelievable blend of vintage shops, independently owned boutiques, and luxury home goods and beauty products.

LINCOLN PARK

Urbs in horto, Chicago's motto meaning "City in a Garden" truly comes to life in the Lincoln Park Neighborhood. Handsome brick row houses and quite tree lined residential areas give way to the more bustling business corridors of the neighborhood like Armitage Avenue brimming with independant boutiques and high end retailers; or Clark Street packed with casual cafes that spill out onto the sidewalks during warmer weather.

 
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EAT

Sometimes you stumble upon a gem without doing any research at all. That's exactly how we found Cupitol, an unassuming little European style cafe who's food quality will surprise you.

Drawn in by the comfy lounge style seating and a bakery case lined with every imaginable pastry your little heart can lust over, Brookklyn and I settled in to order. There is something for absolutely everyone on the massive (and affordable) menu from sustainable free range meats, sandwiches, Gnocchi and vegan dishes. I ordered the Sweet Potato Bowl ($9), chock full of brown rice, kale and coconut curry topped with a poached egg, while Brookklyn became intimately aquatinted with their Avocado Wrap ($7), the griddled whole wheat tortilla overflowing with scrambled eggs, guacamole, queso fresco and pico de gallo. Our first meal in Chicago was rustic and delicious and the sugar and espresso high from the Freddo Cappuccino and Nutella Latte we sipped helped quench the last fragments of travel fatigue we were feeling.

 
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SNACK

While strolling through the historic tree-lined neighborhood of Lincoln Park, we popped into Jeni's to grab a cone. Boasting orgininal flavors like Boozy Eggnog and Brandied Banana Brûlée Jeni's ice creams are unique in both their flavor, smoothness in texture and buttercream body. They even offer dairy free alternatives. I licked my way through their sweet potato with torched marshmallow flavor while Brookklyn enjoyed a dairy-free dark chocolate truffle scoop.

 
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SEE

Drunk with the magic of the city (and maybe a few glasses of Buffalo Trace) Brookklyn and I took in the stimulating cabaret-style variety show aptly coined Unbridled, that takes place every Thursday night at the Untitled Super Club. Praised as a contemporary revival of a classic Prohibition-era Chicago supper club, the late night lounge serves the largest curated selection of American whiskeys anywhere…over 500 and counting. With a cocktail menu as provocative as their show, we snagged one of the few remaining spots left at the bar, ordered drinks and settled in for the show.

The burlesque show went down smooth (just like the Whiskey neat I'd ordered) on a small stage that made it feel like the show was just for me. After the first act, the Cabaret had me longing for the gold old days of Prohibition. Almost.

 
 
 
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Decorated cocktails floated around the room ordered by several shy, love-locked sweethearts all smiling and clapping towards the dance floor. When the show ended the audience was invited up on the stage for dancing. Setting my own old fashioned down, I hopped up on stage and sashayed around the dance floor in pure, uninhibited joy. Moments later, Brookklyn joined in and the two of us cackled and twirled in a blur of long loose hair. Channeling my inner Carrie Bradshaw, I let the beat of Cheryl Lynn's Got To Be Real dictate my steps as the rosy cheeked crowed continued to clapped politely until the songs end and the battle cry for last call reverberated through the parlor's champaign dinning room.

 
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Back at Holiday Jones, I kicked off my heels and continued with a dance party-for-one, while Brookklyn whipped up a late night vegan snack in the complementary chef's kitchen. We stumbled back up to our room and slipped sleepily into bed. I stretched my limbs across the crisp, soft sheets, nestled my head deep into the oversized down pillow and let the sound of the "L" rattling on in the distance just outside our window lull me to sleep.

 
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DAY TWO

The next morning found us both refreshed and ready to explore. We began the day with fresh Argentinian mushroom thyme and blue cheese empanadas from 5411 and the essential accompaniment to any good breakfast—turmeric soy lattes from the hostel's in house cafe. With full stomachs, we caught up on emails and even made friends with the studious pair sitting next to us, who also happened to be wedding photographers.

 
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Special thanks to  Hannah Foldy  for capturing this photo of Brookklyn and I—together—in the same frame!

Special thanks to Hannah Foldy for capturing this photo of Brookklyn and I—together—in the same frame!

 

EAT

"Meat Free Since '83." That's the motto at the touted Chicago Diner, and this vegan paradise stays true to its mission, providing delicious, eco-conscious eats. It's not healthy food. It's diner comfort food and while there are far better vegan options in Chicago in my opinion, this is the place to bring people to PROVE you can do it without meat.

The menu at The Chicago Diner is as sizable as the portions they dish out and the options range from milk-free milkshakes, to meat-free Ruban's, and even egg-free scrambled eggs.

 
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After perusing the menu we ordered the Thai Chili Wings as a starter and a Rosemary Citrus soda for me and a Lavender Lemonade for Brookklyn. The voodoo magic they're able to re-create with their seitan wings is a testament to the dedication of making meat substitutes taste good. With a chili lime marinade and Sriracha Ranch dipping sauce these wings were like meat falling off the bone. Tender, soft, the perfect texture, (or at least from what I can remember meat tasting like after being vegetarian for 15 years) I had to resist the urge to grab the entire plate and run away with it. It was difficult but with a plethora more to choose from on the menu, I somehow managed.

Hearty appetites lead us to ordering the Pierogi Quesadilla, the Cuban Sandwich, and a whopping plate of Poutine (Have you ever known me to pass up potatoes??) for Entrees.

Filled with sauerkraut, mashed potatoes, sautéed mushrooms, onions and Daiya cheese, the Pierogi Quesadilla was a bit of a disappointment. This is one item I'd skip when ordering in the future. The Poutine was a bit misleading and while it didn't come with waffle fries as advertised, it was topped with melted "Teese" (their vegan alternative to nacho cheese) and loaded with country gravy and green onions. In true Rachel fashion, I had to pay homage to my spudded lover, and me and my seething plate of potatoes headed outside for our closeup. The Cuban however was mouthwateringly delicious. Consisting of breaded chicken-style seitan, roasted red bell peppers, melted "Teese", and arugula, this humble sandwich served on a crunchy ciabatta was bursting with flavor.

 
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We ended our whirlwind adventure with a stroll through Chicago's beautiful Riverwalk. Since it's transformation into a recreational destination, the Riverwalk has been a bustling hub of activity that weaves the life of the River into the urban fabric of the city. The fetid stench of the river and its dregs was overtaken by the wafting scents from the nearby Bloomer chocolate factory on W. Kinzie Street and as we marveled at the magnificent views the aroma of hot chocolate lingered just long enough for me to feel like I could taste it.

The city of Chicago is a city that always leaves me hungry for more and while my wanderlust was satiated this time around, I know it's only a matter of time until I return for more.

 
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